3-(2,4-Dichloro-benzyl-idene)-1,5-dioxa-spiro-[5.5]undecane-2,4-dione.

In the title mol-ecule, C(16)H(14)Cl(2)O(4), the 1,3-dioxane and cyclo-hexane rings exhibit distorted boat and chair conformations, respectively. In the crystal, a pair of weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into an inversion dimer.

Related literature

For ring puckering parameters, see: Cremer & Pople (1975 ▶). For related structures, see: Zeng (2011a ▶,b ▶).

Experimental

Crystal data

C16H14Cl2O4

M = 341.17

Triclinic,

a = 7.2378 (6) Å

b = 7.6496 (7) Å

c = 14.8099 (13) Å

α = 100.569 (2)°

β = 100.870 (2)°

γ = 99.050 (1)°

V = 775.80 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 298 K

0.24 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.903, T max = 0.934

4085 measured reflections

2697 independent reflections

1596 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.073

S = 1.01

2697 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016813/is2706sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016813/is2706Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016813/is2706Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H14Cl2O4	Z = 2
Mr = 341.17	F(000) = 352
Triclinic, P1	Dx = 1.461 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2378 (6) Å	Cell parameters from 1133 reflections
b = 7.6496 (7) Å	θ = 3.0–26.3°
c = 14.8099 (13) Å	µ = 0.43 mm−1
α = 100.569 (2)°	T = 298 K
β = 100.870 (2)°	Block, colorless
γ = 99.050 (1)°	0.24 × 0.22 × 0.16 mm
V = 775.80 (12) Å3

Bruker SMART CCD area-detector diffractometer	2697 independent reflections
Radiation source: fine-focus sealed tube	1596 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.903, Tmax = 0.934	k = −9→8
4085 measured reflections	l = −15→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0188P)2] where P = (Fo2 + 2Fc2)/3
2697 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.24503 (11)	1.26534 (9)	0.42676 (5)	0.0765 (3)
Cl2	0.26105 (12)	1.05072 (12)	0.75170 (5)	0.0981 (3)
O1	0.0537 (2)	0.4031 (2)	0.21259 (10)	0.0524 (4)
O2	0.1859 (2)	0.5715 (2)	0.11368 (10)	0.0544 (4)
O3	−0.0445 (2)	0.5412 (2)	0.33392 (12)	0.0641 (5)
O4	0.2444 (3)	0.8711 (2)	0.14747 (12)	0.0737 (6)
C1	0.0566 (4)	0.5535 (3)	0.27859 (17)	0.0477 (6)
C2	0.1771 (3)	0.7246 (3)	0.27024 (16)	0.0446 (6)
C3	0.2092 (4)	0.7332 (4)	0.17488 (18)	0.0542 (7)
C4	0.1872 (3)	0.4094 (3)	0.15131 (15)	0.0475 (6)
C5	0.1083 (4)	0.2509 (3)	0.06858 (15)	0.0590 (7)
H5A	−0.0152	0.2648	0.0348	0.071*
H5B	0.0890	0.1396	0.0911	0.071*
C6	0.2453 (5)	0.2383 (4)	0.00165 (18)	0.0758 (9)
H6A	0.1968	0.1292	−0.0477	0.091*
H6B	0.2497	0.3416	−0.0278	0.091*
C7	0.4462 (5)	0.2341 (4)	0.0524 (2)	0.0789 (9)
H7A	0.5305	0.2360	0.0087	0.095*
H7B	0.4447	0.1222	0.0745	0.095*
C8	0.5242 (4)	0.3952 (4)	0.13604 (18)	0.0693 (8)
H8A	0.5420	0.5064	0.1133	0.083*
H8B	0.6483	0.3829	0.1699	0.083*
C9	0.3869 (3)	0.4063 (3)	0.20302 (16)	0.0540 (7)
H9A	0.3826	0.3025	0.2322	0.065*
H9B	0.4343	0.5152	0.2525	0.065*
C10	0.2437 (3)	0.8767 (3)	0.33824 (16)	0.0504 (6)
H10	0.2987	0.9759	0.3175	0.060*
C11	0.2451 (3)	0.9140 (3)	0.43884 (16)	0.0466 (6)
C12	0.2502 (3)	1.0907 (3)	0.48706 (18)	0.0499 (6)
C13	0.2546 (3)	1.1339 (3)	0.58226 (18)	0.0583 (7)
H13	0.2557	1.2523	0.6122	0.070*
C14	0.2571 (4)	0.9983 (4)	0.63227 (17)	0.0614 (7)
C15	0.2579 (4)	0.8223 (4)	0.58863 (18)	0.0626 (7)
H15	0.2625	0.7323	0.6231	0.075*
C16	0.2516 (3)	0.7824 (3)	0.49329 (17)	0.0556 (7)
H16	0.2518	0.6639	0.4641	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.0930 (6)	0.0474 (4)	0.0950 (5)	0.0228 (4)	0.0231 (4)	0.0214 (4)
Cl2	0.1014 (7)	0.1296 (8)	0.0606 (5)	0.0288 (6)	0.0176 (4)	0.0099 (5)
O1	0.0548 (12)	0.0464 (10)	0.0572 (10)	0.0053 (8)	0.0212 (9)	0.0094 (8)
O2	0.0702 (13)	0.0456 (10)	0.0496 (9)	0.0117 (9)	0.0128 (9)	0.0161 (9)
O3	0.0681 (13)	0.0590 (12)	0.0697 (12)	0.0082 (10)	0.0341 (11)	0.0100 (10)
O4	0.1040 (17)	0.0512 (12)	0.0730 (13)	0.0128 (11)	0.0244 (11)	0.0288 (10)
C1	0.0491 (17)	0.0479 (16)	0.0474 (15)	0.0122 (13)	0.0102 (13)	0.0121 (13)
C2	0.0489 (16)	0.0360 (14)	0.0520 (15)	0.0104 (12)	0.0141 (13)	0.0126 (12)
C3	0.0559 (18)	0.0515 (17)	0.0574 (17)	0.0132 (14)	0.0092 (14)	0.0189 (15)
C4	0.0528 (17)	0.0466 (15)	0.0479 (14)	0.0090 (13)	0.0178 (13)	0.0166 (12)
C5	0.070 (2)	0.0499 (16)	0.0520 (15)	0.0002 (14)	0.0152 (14)	0.0059 (13)
C6	0.103 (3)	0.0626 (19)	0.0573 (17)	−0.0016 (18)	0.0341 (18)	0.0017 (15)
C7	0.088 (3)	0.072 (2)	0.090 (2)	0.0206 (18)	0.051 (2)	0.0148 (18)
C8	0.059 (2)	0.0699 (19)	0.0822 (19)	0.0148 (16)	0.0238 (16)	0.0149 (17)
C9	0.0538 (18)	0.0544 (16)	0.0552 (15)	0.0125 (13)	0.0128 (14)	0.0135 (13)
C10	0.0478 (17)	0.0459 (16)	0.0642 (17)	0.0165 (13)	0.0163 (13)	0.0191 (14)
C11	0.0400 (16)	0.0424 (15)	0.0575 (16)	0.0100 (12)	0.0089 (12)	0.0117 (13)
C12	0.0423 (16)	0.0448 (15)	0.0614 (16)	0.0100 (12)	0.0090 (12)	0.0103 (13)
C13	0.0466 (17)	0.0541 (17)	0.0687 (18)	0.0129 (13)	0.0097 (14)	0.0008 (15)
C14	0.0440 (18)	0.076 (2)	0.0596 (17)	0.0110 (15)	0.0103 (13)	0.0060 (16)
C15	0.0577 (19)	0.070 (2)	0.0611 (18)	0.0108 (15)	0.0078 (15)	0.0236 (16)
C16	0.0557 (18)	0.0443 (15)	0.0623 (17)	0.0084 (13)	0.0069 (14)	0.0086 (14)

Cl1—C12	1.739 (2)	C7—C8	1.526 (3)
Cl2—C14	1.734 (2)	C7—H7A	0.9700
O1—C1	1.361 (3)	C7—H7B	0.9700
O1—C4	1.446 (2)	C8—C9	1.532 (3)
O2—C3	1.358 (3)	C8—H8A	0.9700
O2—C4	1.450 (2)	C8—H8B	0.9700
O3—C1	1.203 (2)	C9—H9A	0.9700
O4—C3	1.206 (3)	C9—H9B	0.9700
C1—C2	1.493 (3)	C10—C11	1.462 (3)
C2—C10	1.346 (3)	C10—H10	0.9300
C2—C3	1.485 (3)	C11—C12	1.400 (3)
C4—C5	1.507 (3)	C11—C16	1.402 (3)
C4—C9	1.509 (3)	C12—C13	1.381 (3)
C5—C6	1.530 (3)	C13—C14	1.382 (3)
C5—H5A	0.9700	C13—H13	0.9300
C5—H5B	0.9700	C14—C15	1.383 (3)
C6—C7	1.514 (4)	C15—C16	1.379 (3)
C6—H6A	0.9700	C15—H15	0.9300
C6—H6B	0.9700	C16—H16	0.9300
C1—O1—C4	119.82 (19)	H7A—C7—H7B	108.0
C3—O2—C4	118.34 (17)	C7—C8—C9	111.0 (2)
O3—C1—O1	118.7 (2)	C7—C8—H8A	109.4
O3—C1—C2	125.7 (2)	C9—C8—H8A	109.4
O1—C1—C2	115.4 (2)	C7—C8—H8B	109.4
C10—C2—C3	117.0 (2)	C9—C8—H8B	109.4
C10—C2—C1	126.3 (2)	H8A—C8—H8B	108.0
C3—C2—C1	116.4 (2)	C4—C9—C8	111.23 (19)
O4—C3—O2	118.8 (2)	C4—C9—H9A	109.4
O4—C3—C2	124.9 (2)	C8—C9—H9A	109.4
O2—C3—C2	116.2 (2)	C4—C9—H9B	109.4
O1—C4—O2	108.91 (17)	C8—C9—H9B	109.4
O1—C4—C5	106.67 (19)	H9A—C9—H9B	108.0
O2—C4—C5	106.30 (18)	C2—C10—C11	131.6 (2)
O1—C4—C9	111.22 (17)	C2—C10—H10	114.2
O2—C4—C9	110.75 (19)	C11—C10—H10	114.2
C5—C4—C9	112.76 (19)	C12—C11—C16	116.3 (2)
C4—C5—C6	111.0 (2)	C12—C11—C10	120.1 (2)
C4—C5—H5A	109.4	C16—C11—C10	123.5 (2)
C6—C5—H5A	109.4	C13—C12—C11	122.5 (2)
C4—C5—H5B	109.4	C13—C12—Cl1	117.25 (19)
C6—C5—H5B	109.4	C11—C12—Cl1	120.21 (19)
H5A—C5—H5B	108.0	C12—C13—C14	118.8 (2)
C7—C6—C5	111.9 (2)	C12—C13—H13	120.6
C7—C6—H6A	109.2	C14—C13—H13	120.6
C5—C6—H6A	109.2	C13—C14—C15	121.0 (2)
C7—C6—H6B	109.2	C13—C14—Cl2	119.2 (2)
C5—C6—H6B	109.2	C15—C14—Cl2	119.8 (2)
H6A—C6—H6B	107.9	C16—C15—C14	119.0 (2)
C6—C7—C8	111.6 (2)	C16—C15—H15	120.5
C6—C7—H7A	109.3	C14—C15—H15	120.5
C8—C7—H7A	109.3	C15—C16—C11	122.3 (2)
C6—C7—H7B	109.3	C15—C16—H16	118.8
C8—C7—H7B	109.3	C11—C16—H16	118.8
C4—O1—C1—O3	−173.9 (2)	C6—C7—C8—C9	54.4 (3)
C4—O1—C1—C2	10.6 (3)	O1—C4—C9—C8	174.74 (18)
O3—C1—C2—C10	23.5 (4)	O2—C4—C9—C8	−64.0 (2)
O1—C1—C2—C10	−161.3 (2)	C5—C4—C9—C8	55.0 (3)
O3—C1—C2—C3	−149.8 (2)	C7—C8—C9—C4	−54.3 (3)
O1—C1—C2—C3	25.3 (3)	C3—C2—C10—C11	−176.9 (2)
C4—O2—C3—O4	166.2 (2)	C1—C2—C10—C11	9.8 (4)
C4—O2—C3—C2	−17.3 (3)	C2—C10—C11—C12	−154.4 (2)
C10—C2—C3—O4	−19.7 (4)	C2—C10—C11—C16	29.0 (4)
C1—C2—C3—O4	154.3 (2)	C16—C11—C12—C13	−2.2 (4)
C10—C2—C3—O2	164.1 (2)	C10—C11—C12—C13	−179.0 (2)
C1—C2—C3—O2	−21.9 (3)	C16—C11—C12—Cl1	179.42 (17)
C1—O1—C4—O2	−47.4 (2)	C10—C11—C12—Cl1	2.6 (3)
C1—O1—C4—C5	−161.76 (18)	C11—C12—C13—C14	1.1 (4)
C1—O1—C4—C9	74.9 (2)	Cl1—C12—C13—C14	179.48 (19)
C3—O2—C4—O1	51.0 (3)	C12—C13—C14—C15	0.8 (4)
C3—O2—C4—C5	165.5 (2)	C12—C13—C14—Cl2	−179.59 (19)
C3—O2—C4—C9	−71.6 (2)	C13—C14—C15—C16	−1.4 (4)
O1—C4—C5—C6	−176.71 (19)	Cl2—C14—C15—C16	178.97 (19)
O2—C4—C5—C6	67.2 (3)	C14—C15—C16—C11	0.2 (4)
C9—C4—C5—C6	−54.3 (3)	C12—C11—C16—C15	1.6 (4)
C4—C5—C6—C7	53.8 (3)	C10—C11—C16—C15	178.3 (2)
C5—C6—C7—C8	−54.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3i	0.93	2.50	3.286 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3i	0.93	2.50	3.286 (3)	143

Symmetry code: (i) .